I think it has aged well enough because of the cyberpunk aesthetic. I watched it the other day and the first movie (with its seamless mix of philosophy, action, and cyberpunk dystopia) as well as the freeway chase/fight of the second movie has held up extremely well.
If Wachowski can go back to basics with the 4th film by taking the cue from the first film, it may well be a return to form for the series and Wachowski.
Yes, they will have to try a different approach to make an impact. Film-Noire, Screwball Comedy, Musical? Okay, those are a little extreme [but who wouldn't see a Matrix musical?].
For me, the aesthetic is one of the things that aged badly. For me, those trenchcoats and MIBs scream 80s and 90s. Bullet Time has become a cliche for all the right reasons, it was amazing the first time you saw it, but special effects are far more
special now. I think the philosophy is too upfront and really shallow. It is trying [again for my liking] too hard to be profound and comes across as a P K Dick pastiche. I think he does it so much better and usually way-down in the subtext so that its a homer.
One remake/reboot/sequel I am looking forward to is the new Top Gun. The first one is a terrible but fun film and Cruise has promised no CGI in the flying and I'd like to see some more
need for speed filmed with new technology.